THE PLAY’S THE THING
A splendid, and somewhat overlooked, movie from 1999 is Topsy-Turvy, an entertaining biography of the famous operetta composers, Gilbert and Sullivan. It is also a fascinating look backstage at the world of theater and a delightful glimpse at the rigors of writing and producing for the stage. Any movie fan interested in the components of live theater will adore Topsy-Turvy.
Al Pacino’s lifelong infatuation with Shakespeare’s Richard III provides the basis for the intelligent and riveting Looking For Richard (1996). With a few of his friends (Kevin Spacey, Winona Ryder, Estelle Parsons, Aidan Quinn, et al) Pacino first dissects a scene, relates it to modern life, then the cast performs it. Another wonderful film for anyone interested in the theater, Shakespeare- or life.
A variation on this theme is the remarkable Vanya On 42nd Street (1994) in which we watch the actors, director and small audience experience Chekov’s Uncle Vanya. Director Louis Malle’s version of David Mamet’s play is almost hypnotic as we watch the actors become the characters and the rehearsal become the play, and both somehow become real life. Wallace Shawn, Andre Gregory and Julianne Moore head a fine cast. 
Woody Allen’s Bullets Over Broadway (1994) is his take on the creative process involved in live theater. Diane Wiest (Oscar, best supporting actress), John Cusak, Chaz Palmienteri, and Jennifer Tilly have a ball in this constantly funny and engaging film. Cusak is a struggling playwright who sells out in a heartbeat to get his 
play produced, even if involves placating the mob and casting their moll as the heroine. One of Woody’s delightful entertainments, without a serious bone in its body.
Shakespeare In Love (1998) brought the Bard to the masses, enchanted everyone with its humor and heart, and won the Oscar for best movie. Gwyneth Paltrow (Oscar), Joseph Fiennes, Judy Dench (Oscar) and Geoffrey Rush gleefully lead this romp through 16th century theater. Shakespeare decides against “Romeo and Ethel” as a title, and decides to leave out the pirates in his latest play. He also strives to get paid rather than to get famous.
Annette Bening owns Being Julia (2004) lock, stock and barrel, but that’s ok because she is absolutely super as an aging actress who still knows a trick or two. She seems always “on stage” to her college-aged son and her producer-husband (Jeremy Irons). She is roughly pushed aside by a director and young ingenue. Then she pushes back!
All of the films in this article are available on DVD. All are suitable for children 12 and over.